My Worst Investment Ever Podcast

• Why Family Businesses Stay Stuck in Survival Mode

  I once worked with a family business run by two brothers and a sister. The sister was a dreamer, pushing niche markets and creative ideas. Her CEO brother was all about landing big accounts to keep cash flowing. Every strategy meeting turned into a shouting match. Nothing got decided, and the business was stuck.I pulled the creative sister aside and asked, “Do you want to be CEO?” She laughed, “No way.” That honesty was a game-changer. They finally aligned behind one leader, and the chaos started to fade. Is your family business stuck because no one’s steering the ship?Download The Profit Gap for free at TheProfitBootCamp.com to see 5 hidden reasons family businesses work hard but still fall short of profit.Survival mode kills profitFamily businesses are special, but they come with unique traps. The daily grind, orders, payroll, and customer complaints can bury any chance of big-picture thinking. You’re so busy keeping the lights on that you forget to ask: where’s this business going? That’s survival mode, and it’s a profit killer. Strategy takes a backseat when you’re just trying to get through the week.Clear roles fix family chaosThen there’s the family dynamic. Loyalty and emotions can cloud tough calls. Maybe your cousin’s great at sales but terrible at managing people, yet no one says anything because he’s family. Or your parents are still on the payroll, even though they retired years ago. These are human issues, but they hurt your bottom line.The fix? Write down everyone’s roles, even if it’s awkward. Be clear: who’s in charge of what? I’ve seen families transform their businesses just by putting this on paper. It’s not about cutting people out but giving everyone a lane so the company can move forward. Always return to the core principle that increasing profit increases value for all family members.If every week feels like a scramble, you’re missing structure. Without a precise rhythm, you’re starting from zero every Monday. That’s exhausting, and it keeps you stuck. Try this: start one monthly owner profit check-in, 60 minutes max.Focus on one question: what’s driving profit next month? It could be following up on late invoices, cutting a small cost, or pushing a high-margin product. Get your team thinking about profit, not just staying busy. Structure turns chaos into progress.Family businesses also risk getting too comfortable. You might have a warm and loyal culture, but is it driving growth? Or is it just keeping the peace? Ask yourself: does our setup push us toward profit, or are we coasting on familiarity?One family business I know kept a low-margin product line because it was “part of our history.” Dropping it felt like betraying the past, but it freed up cash for marketing that doubled their revenue. Logic has to win.Structure over stressHere’s a quick story. I had a client who groaned, “Mondays are a mess.” Projects stalled, and he was micromanaging everything. We set a simple rhythm: Monday to set goals, Wednesday for updates, Friday to review wins. In just a few weeks, his team started owning their tasks. He wasn’t carrying the whole business anymore; he had breathing room. Structure doesn’t sound sexy, but it’s a game-changer.Now you see the real traps keeping your family business stuck. But what if the real problem isn’t your family, it’s you? In our next episode, we’ll face the hard truth about leadership and profit. Don’t miss it.Actions from prior episodesCut one cost: Block 30 minutes, review P&L, and cut one expense. Just one. Lead by example.Find one drain: Review finances weekly, searching for one hidden loss. Act now.The next actionAlign the family: Hold a...

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• Jeff Holman - The Franchise Bubble That Burst Too Soon

  BIO: Jeff Holman, founder of Intellectual Strategies, is revolutionizing legal support for startups and scaling businesses. His Fractional Legal Team model provides expert legal guidance without the cost of a full-time team.STORY: Jeff started a cold plunge and sauna business during the pandemic. The company looked great, but he had employee issues, which affected its success. Soon, tens of other studios, brands, and franchises were all popping up within a mile of Jeff’s studio.LEARNING: Create strategic alignment incrementally and iteratively. “Create strategic alignment incrementally and iteratively because the business that you’re operating today might not be the business that you pivot to tomorrow.”Jeff Holman Guest profileJeff Holman, founder of Intellectual Strategies, is revolutionizing legal support for startups and scaling businesses. His Fractional Legal Team model provides expert legal guidance without the cost of a full-time team. With expertise in engineering, law, and business, Jeff helps companies navigate complex challenges, enabling them to grow with confidence.Worst investment everDuring the COVID-19 pandemic, Jeff decided to find ways to spend his time and invest some of his money. He settled on a cold plunge and sauna business. The spreadsheet looked great, and the numbers were fantastic. The business model followed another business that Jeff had previously done, which had achieved considerable success.Jeff found a local company in Utah that was manufacturing cold plunges at the time and secured a couple of investor friends to invest in the business. He rented an office space and converted one of the suites into a cold plunge and sauna studio.The biggest mistake that cost Jeff this business was hiring employees and trying to get them more involved in marketing. He would help train and incentivize employees, ensure tasks were completed, have people submit reports, follow up for accountability, and more. It felt like he was babysitting his employees. This eventually brought his business down. However, the final nail in the coffin was a proliferation of other studios, brands, and franchises, all popping up within a mile of Jeff’s studio.Lessons learnedIf you’re part of a franchise, consider visiting other franchise businesses that may not be competing with yours or those a little further away from your customer base to observe how they operate.If you’re pivoting your business, create strategic alignment incrementally and iteratively because the business you’re operating today might not be the one you pivot to tomorrow.Andrew’s takeawaysFind a business that does what you want to do in another state and go work with them for a while.Actionable adviceValidate the business idea you want to invest in well beyond the spreadsheet. Research regulations, test your MVP, identify channels that you’ll use to drive revenue, and much more.Jeff’s recommended resourcesJeff’s journey has taught him the value of seeking expert advice. He recommends holding a strategy call with him if you need legal expertise to scale your business confidently. He also suggests reading Rocket Fuel and Traction: Get a Grip on Your Business by Gino Wickman to learn how to align intellectual property, assets, patents, trademarks, and...

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• Delay Fixing Profit and the Hole Gets Deeper

  I met a family business owner in the Philippines who was proud of his “stable” company. Two percent net profit, year after year. Sounds okay, right? Until I showed him the math: because his margin was deeply below average, he’d missed out on $1.2 million in potential profit over three years.That “stability” was a slow bleed, draining his business while he didn’t even notice. Are you losing money you can’t see? That’s what this episode is all about: how profit problems silently grow while you’re looking the other way.Download The Profit Gap for free at TheProfitBootCamp.com to see 5 hidden reasons family businesses work hard but still fall short of profit.Small leaks, big lossesProfit problems don’t usually hit you like a freight train. They creep in quietly; a slight inefficiency here, a missed opportunity there. Maybe it’s a subscription you forgot to cancel or pricing that hasn’t budged in years. These leaks add up, and the longer you wait, the harder they are to fix. Think of it like a leaky pipe: today’s drip becomes a flood tomorrow.The longer you delay, the more risk and complexity you’re piling on. Your margins shrink, your stress grows, and suddenly, you’re vulnerable to a bad month or a competitor’s move. I experienced this in my own business leading up to the government COVID lockdowns.The good news? You don’t need a massive overhaul to start. Just find one recurring cost that’s dragging you down. It could be an overpriced vendor, software you barely use, or a process that wastes your team’s time.One client I worked with found $1,500 monthly in unused cloud storage. Cutting it took 10 minutes and saved him $18,000 a year. That’s the kind of win you can grab right now. Small tweaks today prevent painful losses tomorrow.Don’t overthink, just reviewHere’s a simple way to start: schedule a 30-minute profit review this month. Pull your profit and loss statement and look for one leak. Don’t overcomplicate it. Just ask: where’s money slipping away?If you don’t know your P&L, ask your accountant to walk you through it. You may need a new accountant if your accountant can’t do that. This isn’t about being a finance wizard but knowing your business. One owner I know avoided his financials for years, trusting his bookkeeper. When we finally looked, we found $40,000 lost to outdated pricing. A 30-minute review fixed it. That’s the power of paying attention.Don’t wait until you’re desperate. I’ve seen too many owners hold off until they’re scraping by, thinking they’ll fix profit when things “calm down.” Spoiler: things don’t calm down. The time to act is now when you still have options. If you wait until you’re broke, your choices shrink fast. You might have to cut staff, take a loan, or close up shop. Acting early keeps you in control.Here’s a question to spark clarity: if a third party bought your business today, what’s the first thing they would fix?Maybe it’s a product line barely breaking even or a client who pays late but demands your time. Write down one fix and tackle it this week. That mindset, seeing your business with fresh eyes, uncovers profit you didn’t know you had. Don’t wait for the third party to arrive. Fix your business now.See your business with fresh eyesLet’s pause for a story. I worked with a client who never tracked profit by product. His team was convinced their manufactured products were the cash cow, way better than their imported products. We dug into the numbers, and guess what?The imported products they sold were nearly twice as profitable. He immediately shifted strategy, focused on imports, raised prices on the manufactured stuff, and boosted gross profit by 17% in three months. That money was sitting there, waiting to be found. What’s hiding in your...

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• Enrich Your Future 31: Risk vs. Uncertainty: The Investor’s Blind Spot

  In this episode of Enrich Your Future, Andrew and Larry Swedroe discuss Larry’s new book, Enrich Your Future: The Keys to Successful Investing. In this series, they discuss Chapter 31: The Uncertainty of Investing.LEARNING: Equity investing is always about uncertainty. “Most investors think of investing as much more like risk and forget there’s a lot of uncertainty. That’s a problem because investing is always about uncertainty. You have to recognize that we cannot rely on historical data to tell us that much about the future.”Larry Swedroe In this episode of Enrich Your Future, Andrew and Larry Swedroe discuss Larry’s new book, Enrich Your Future: The Keys to Successful Investing. The book is a collection of stories that Larry has developed over 30 years as the head of financial and economic research at Buckingham Wealth Partners to help investors. You can learn more about Larry’s Worst Investment Ever story on Ep645: Beware of Idiosyncratic Risks.Larry deeply understands the world of academic research and investing, especially risk. Today, Andrew and Larry discuss Chapter 31: The Uncertainty of Investing.Chapter 31: The Uncertainty of InvestingIn this chapter, Larry explains the difference between risk and uncertainty. He highlights that one of the most important concepts to grasp is that investing is about dealing with both risk and uncertainty.University of Chicago professor Frank Knight defined risk and uncertainty as follows: Risk is present when future events occur with measurable probability. Uncertainty is present when the likelihood of future events is indefinite or incalculable. Larry further explains that risk involves known probabilities, like casino odds or life insurance estimates, while uncertainty involves unknown outcomes, such as major events like the Great Depression or COVID-19.Larry explains that we sometimes know the odds of an event occurring with certainty. For example, because of demographic data, we can reasonably estimate the odds that a 65-year-old couple will have at least one spouse live beyond 90. However, we cannot know the exact odds because future advances in medical science may extend life expectancy. Conversely, new diseases may arise that shorten life expectancy.Why must you understand the difference between risk and uncertainty?Larry insists that it is crucial to understand the difference between risk and uncertainty. This understanding is key, as many investors mistakenly view equities as closer to risk, where the odds can be precisely calculated. This misconception often arises when economic conditions are favorable. The ability to estimate the odds gives investors a false sense of confidence, leading them to make decisions that exceed their ability, willingness, and need to take risks.However, Larry adds that the perception of equity investing shifts from risk to uncertainty during crises. Since investors prefer risky bets (where they can calculate the odds, like investing in a stable company with a proven track record) to uncertain bets (where the odds cannot be calculated, like investing in a startup with an unpredictable future) when the markets begin to appear to investors to become uncertain, the risk premium demanded rises, and that is what causes severe bear markets.Further, dramatic falls in prices lead to panicked...

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• No One Is Coming to Save Your Business, Do It Yourself

  I want to tell you about a midsize business owner drowning in consultants. He kept hiring them, one after another, each promising to turn things around. They’d show up, drop off a fancy report, and disappear. Meanwhile, his profit stayed flat, his team was overwhelmed, and he barely slept.One night, he was alone in his office, staring at a payroll he wasn’t sure he could cover. That’s when it hit him. He told me, “I realized it’s on me. No one’s coming to save my business.” That moment was his turning point. So, what’s yours?Download The Profit Gap for free at TheProfitBootCamp.com to see 5 hidden reasons family businesses work hard but still fall short of profit.The turning point every owner needsLet’s be real: hoping someone else will fix your problems is tempting. A consultant, a new hire, maybe even some magic software. But here’s the truth: no one will care about your business as much as you do. Consultants can advise, pinpoint blind spots, and maybe even hand you a plan. But if you don’t act, nothing changes.I’ve seen owners spend thousands on experts only to shelve their advice because it felt too hard or the timing wasn’t “perfect.” Waiting for the right moment is a trap. Your business doesn’t have time for that. The problems are piling up: low margins, stressed teams, endless emergencies, they’re not going away on their own. You have to step up.Your calendar tells the truthI know what you’re thinking: “I’m already doing everything I can!” But are you? Pull up your calendar right now. What does it say? If it’s packed with meetings, emails, and putting out fires, you’re probably not leading; you’re reacting.Your calendar tells the truth about your priorities. If there’s no time blocked for profit-focused work, like reviewing your P&L or cutting a bloated expense, you’re not owning the future of your business.One client I worked with swore he had no time for strategy. His calendar showed 12 hours a week chasing emergencies, zero on profit. We carved out just 90 minutes a week to review his financials. Within months, his managers solved problems without him, and the whole business felt calmer and more focused. That’s the power of taking charge.Here’s the thing: you can’t pay someone to care as much as you do. You can hire the best accountant and the sharpest operations manager, but responsibility for your business’s success rests with you.It’s not about working harder; it’s about working smarter. Start small. Pick one profit-related task this week. Maybe it’s canceling an unused subscription, renegotiating a vendor contract, or reviewing your pricing. Do it by Friday. One task, done well, can shift your momentum.A client thought he needed a complete overhaul to boost profit. Instead, we started with one thing: he cut a $900 monthly software he barely used. That small win gave him the confidence to tackle bigger issues.Start small, lead strongYour team is watching you, too. They feed off your clarity and energy. If you’re scattered, putting out fires, they’ll be scattered too. But they’ll follow if you show up focused with a clear plan. That client I mentioned. Whose calendar was filled with firefighting?Once he started those weekly financial reviews, his team noticed. They started coming to meetings prepared, pitching ideas to save money. Your leadership sets the tone. When you own your business’s future, you also allow your team to step up.Owning your business isn’t just about responsibility; it’s your biggest advantage. No one knows your customers, team, or vision like you do. That’s your edge. But you have to use it. Stop waiting for a savior. Stop hoping the market will turn or a new hire will fix everything. The power to change your business is in your hands right now.So, here’s

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